


Cherry

by outoftheashes, Wearingdeantoprom



Category: Supernatural
Genre: Abuse, Anal Fingering, Anal Sex, Angst, Angst and Porn, Banter, Barebacking, Bottom Sam, Collaboration, Coming Untouched, Drinking, Dubious Consent, First Time, Implied/Referenced Alcohol Abuse/Alcoholism, Kinktober, Kinktober 2019, Loss of Virginity, M/M, Mildly Dubious Consent, Other: See Story Notes, Plot What Plot/Porn Without Plot, Pre-Canon, Pre-Series Dean Winchester/Sam Winchester, Pre-Stanford Era (Supernatural), Recreational Drug Use, Shotgunning, Spanking, Top Dean Winchester, Top Dean Winchester/Bottom Sam Winchester, not between Sam and Dean though, the abuse has to do with John in case that wasn't clear
Language: English
Status: Completed
Published: 2019-10-05
Updated: 2019-10-05
Packaged: 2020-11-24 18:50:09
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,834
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20912408
Author URL: https://archiveofourown.org/users/outoftheashes/pseuds/outoftheashes, https://archiveofourown.org/users/Wearingdeantoprom/pseuds/Wearingdeantoprom
Summary: Sam admits he’s going to start drinking in college. Dean doesn’t want Sam’s first time to be in a shady situation, he wants Sam to know how to protect himself - so Dean comes up with the brilliant idea to get them both drunk. Add shotgunning and spanking into the mix and it goes about as well as can be expected.ORThe pre-series pwp that nobody asked for.





	Cherry

**Author's Note:**

> Sam and Dean experience altered mental states due to the alcohol and drugs, which brings into question their ability to consent if this were the real world. But, because this isn’t the real world, we (Tori and Holly) have the power to wave away those issues and say that both boys want this. A lot.
> 
> There is also an ‘abuse’ tag. In this fic, John makes assumptions and threats. He grabs Sam’s wrist during their fight and throws a bottle against a motel wall. I (Tori) see these particular things as abusive in nature. If this bothers you for any reason, feel free to turn back now. 
> 
> There is no strict timeline here because the show is pretty fucking iffy when it comes to pre-series shenanigans. Especially regarding Sam and his time before and during Stanford. All you really need to know is this fic happens before he leaves, and Dean understands that he’s going to leave.
> 
> Written for Kinktober 2019, Day 5: Shotgunning.

"Sammy! Earth to Sam!" Dean says in an annoying sing-song voice.

"Huh?" Sam blinks, putting his book down so he can give Dean his undivided attention. "What's up?"

"Thought we should have the college talk. You know, since Dad's not around." Dean keeps his voice light and friendly but there’s hurt simmering there, too.

Sam gulps and stands up, stretching out his aching muscles. "What about it?"

"There's gonna be a lot of... Grown-up shit there and..." Dean huffs. "Just. You gotta be careful."

“Think I can't hold my own in a fight?" Sam teases gently and moves into Dean's space so he can playfully smack his arm. There’s a void in Sam’s chest, a hole, that he doesn’t know if he can ever fill. Or if he even _wants _it filled. When he leaves, why should anyone get to claim Dean's spot?

"Of course you can,” Dean replies, swatting Sam's hands away. "That's not what I'm talking about."

"Think someone might take advantage of me?" Sam guesses, arching a brow. "I don't think college is as dangerous as you're making it out to be, Dean. Not for a white guy.”

"It is for someone who’s as pretty as you are.”

The compliment is a punch in the gut. A _nice_ punch. His lungs work their damnedest for air, his mouth wide open as he stares at Dean. Trying to figure out what the hell just happened. "Dean." He licks his lips and tries again. "I guess this is a good time to admit I'm probably going to start drinking in college."

"Yeah. That's the issue."

"Why? _You_ drink," Sam points out and crosses his arms. "You started drinking before you were twenty-one, so I hope you aren't trying to talk me out of it."

"No. I'm just telling you to be careful. When at a party or a bar, pour your drink yourself or take it directly from the bartender and never let it out of your sight. Don’t fucking take drinks from anyone. It’s not just girls who get their drinks spiked. Seriously.”

"So, you think I'm pretty but also stupid, huh?" Sam hums thoughtfully. "Don't worry, Dean. I won't accept drinks from anyone."

"We're gonna get drunk tonight.”

"Yeah? And why's that?"

"Well, I figure you should pop your booze cherry before I send you off. Then you know what to expect and you can stay safe."

"My... my booze cherry?" Sam repeats dubiously, his voice cracking, which of course makes his cheeks burn in embarrassment.

Dean chuckles. "Hang tight. I'll go get us some stuff."

Sam breathes easier. He's missed it. Dean laughing like this. It doesn’t even matter that it’s probably at Sam's expense. It’s a nice sound.

"All right," Sam replies softly. "I'll just... keep reading."

Dean glances at the cover of the book and makes a face. "_The Virgin Suicides_? Whatever you say, weirdo."

* * *

About an hour later Dean returns, paper bags in his hands. "Ready to get fucked?"

"Fucked?" Sam asks, inwardly cursing at himself and his stupid voice when it breaks again. "Dude, your word choice needs work. It’s kinda suggestive.”

"I meant fucked up," Dean clarifies, putting the bags down on the table. "On this.” He starts pulling out the bottles.

"Oh." Sam licks his lips. "That's a lot of alcohol, Dean. A bit overkill, don’t you think?"

"We're gonna get you good and wasted," Dean replies with a grin. "And after..." He pulls out a fat joint and places it on the table too.

"Wow." Sam blinks at the weed a few times. He isn't really sure what to say. "Is that a good idea? Doing both in one night?"

"I figured I'd get you drunk and then, if you felt like it, we could smoke this. If not, we can save it."

"Okay, Dean. Show me what to do."

"We're gonna start off slow with some beer," Dean says, popping the tabs on two cans and passes one to Sam.

Sam takes the beer and sniffs it, making a face. "Huh. It smells... not great."

"It's an acquired taste. Kinda like you." Dean grins and pushes Sam's shoulder.

Sam frowns and shoves Dean back. "Rude," he says, laughing. "Speak for yourself."

"I'm fucking awesome." Dean takes a deep gulp of beer.

"You are," Sam says before thinking better of it then follows suit so he won’t say more stupid shit.

"How is it?"

"Pretty gross.”

"Yeah, it is at first. It'll grow on you,” Dean promises. "Come on. That can won't drink itself."

"Really?" Sam complains. It’s all in good fun, though. "Do I have to? I want harder stuff, things I can drink fast."

"You can have hard shit once you down that beer.”

"God, you're so bossy," Sam grumbles then swallows some beer. "Ugh, why do people drink this?"

"Because it’s _good_," Dean replies and finishes his can.

"I don't agree.” Sam empties his can too despite how fucking revolting it is. Apparently, he doesn’t have a choice if he wants the good shit.

"That's my boy," Dean almost purrs and smacks Sam's shoulder. "Next up is Everclear 151.”

"Now we're talking."

Dean pours two shots. "Bottoms up."

"Yeah." Sam takes a glass, albeit slower this time. "How many of these do you think it'll take to fuck me up?"

"Probably two," Dean teases.

"Jerk," Sam pouts at his brother then slams the shot back, taking it in one big gulp. "Oh." He coughs. "That's." His face twists. "Strong."

"See why I started you off easy?" Dean asks, low and soft.

"I guess.”

"Want bourbon next?"

“Isn't it bad to mix your drinks this much?"

“Nah, that’s a myth. Not about _what _you drink but _how much _you drink,” Dean says, pouring a shot.

Sam holds out his hand. "Yeah, yeah. Whatever. Gimme another.”

Dean passes Sam his shot and throws his own back with a little moan.

Sam raises an eyebrow. "Should I give you a minute alone with the bourbon?"

“This is just some really fucking good bourbon."

"Uh-huh..." Sam takes his shot, wrinkling his nose.

“Gin’s next,” Dean says, pouring liquid from a new bottle.

"Did you get us juice? Don’t we need chasers?”

“We can use beer?” Dean offers with a shrug.

"Great," Sam whines dramatically. "I'm gonna get so fucked up. Here's hoping I don't choke on my own vomit and die."

“You won't," Dean replies, suddenly serious. "I'm gonna look after you, Sammy."

“If you look out for me, who's gonna look after you?" Sam asks, just as serious.

“I've got a pretty good tolerance built up. And I’ll stop drinking soon."

"Doesn't sound very fun for you, but okay."

"This isn't about me having fun, Sammy."

Sam points at the joint. "No? So weed isn't fun now?"

Dean rolls his eyes. "Okay, so that will be fun but the point of this is to get some experience with this shit under your belt in a safe place."

“Whatever you say, boss,” Sam says, snorting.

"What?" Dean asks, sliding the gin over to Sam.

"Am I not allowed to laugh now?" Sam’s fingers brush against Dean's as he grabs the shot, still grinning. That amusement leaves his face, however, when he drinks it. "Apparently I'm not drunk enough yet because the alcohol still tastes like ass."

"You didn't like the bourbon?"

“Ah, don't be sad," Sam says, giggling. "Mmmm... More please."

Dean grins. "It’s working,” he says, pouring from yet another bottle.

"Mmmm.” Sam laughs and stands up, doing a silly dance. "A little bit."

“You're getting a little pink in the cheeks," Dean comments. “Cute.”

Sam sucks down the alcohol when it’s offered to him then starts wiggling his ass. "Right. I'm so cute," he says, disbelieving but happy.

"Well, I think it's safe to say you get flirty when drinking,” Dean says, looking up at Sam from where he’s seated at their shitty motel table. "How's the tequila?"

"I guess I do." Sam moves closer to his brother, swaying back and forth. "I like it. I want more of it," he rasps, putting his shot glass on Dean's lap. Right by his crotch.

“Ask nicely, Sam,” Dean says, picking up the glass.

Sam lets out a playful growl. He taps his foot against Dean's. "Why? You're not my daddy."

"No, but I'm your big brother,” Dean replies with a smirk and nudges his foot back against Sam's.

“You weren't making me ask nicely before," Sam points out breathily, his clumsy hands reaching out to mess up Dean's hair.

“Yeah, but you also weren't demanding before," Dean growls, swatting at Sam's hands.

Sam gasps when Dean smacks his hands and his dick twitches. Wow, this is heading into weird territory fast. To say the least. But he’d be lying if he said the attention isn’t thrilling. “So, what? If I'm not a perfect angel you won't give me more?"

“Not a perfect angel. Just polite."

Sam drops down to the ground and nuzzles Dean's knees. "I'd really like some more, Dean. Or we could take a break and try out the weed."

"Jesus, Sam," Dean breathes and promptly gives Sam more tequila.

"Did I do a good job?" Sam asks, a smirk on his lips. He licks the rim of the glass. Is it as obscene as it feels? He hopes so.

"Yeah, Sammy, you did real good."

Sam moans and his cock jerks happily. He lays his free hand on Dean's thigh, gripping it, then sucks his drink down. "This is fun."

"It sure is." Dean tosses back another drink then pours yet another glass for Sam.

Sam hums, nuzzling Dean's knees again. "So you don't wanna smoke with me? Or you do?"

"I do," Dean says. He holds the glass to Sam's mouth. "Have you had weed before?"

Sam shivers, warmth flooding his body as he tilts his head back slightly. "No. Have you?"

"Yeah." Dean pours the shot into Sam's mouth carefully. "Don't worry, I'll teach you."

"Where? Here? Or on a bed?" Sam rasps, flicking his tongue against his teeth as he watches his brother.

"The bed," Dean says quickly.

"When, Dean? I really fucking want to."

"Come on. Let's do it now."

"Help me up?"

Dean rolls his eyes and stands before reaching down to easily pull Sam to his feet.

Sam wraps his arms around Dean to steady himself. "Don't get cranky."

Dean smiles and runs his fingers through Sam's hair. "M'not," he says and reaches for the joint, lighter, and tequila then maneuvers Sam to the bed.

Sam's dick likes getting pushed around far too much. He likes Dean's fingers in his hair even better. "I missed your smile, Dean," Sam blurts, too drunk to keep his ridiculous thoughts to himself. "Looks so good on you."

"Yeah?" When Sam sits, Dean plops down next to him.

"Yes.” Sam leans against his brother. His fingers wander to the amulet around Dean's neck, the one Sam gave to him when he was small. He strokes it gently. "Okay, I'm ready. Light the joint."

Dean does, taking a few deep puffs. "It'll make your lungs burn at first so be gentle," he says and places the joint in Sam’s hand.

Sam tries to be gentle but as soon as he inhales he coughs anyway. "Ow, fuck," he says, frowning as he hands the weed back to Dean. "Hurts."

Dean pats Sam's back. "It's easier if you take the smoke from someone else. They take the brunt of the burn."

"Can you do that with me?"

"Yeah, I can. I'm going to take a deep hit and then when I blow it out, you gotta put your mouth near mine and breathe in, okay?"

Sam hums thoughtfully then moves so close to his brother that their lips damn near touch. "Like this?"

"Yeah," Dean rasps. He takes a deep pull of the joint then leans in close to Sam to give him the smoke.

Sam inhales greedily. It still burns, but it's much more pleasant this time. He moans as the smoke drifts out of his mouth. "Much better."

"Wanna try again?

Sam playfully smacks Dean's arm, totally unnecessary and flirty. "Obviously."

Dean takes a deeper hit, then leans in to give Sam the smoke from his lungs. Sam's lips barely brush against Dean's. "I think I like this better than drinking."

Dean moans softly. "Yeah?"

Sam's breath hitches and he nods. "Can we smoke the whole thing?"

Dean traces his thumb along Sam's jawline. "Yeah, 'course we can. Wanna try it straight from the joint again?"

Sam pushes into Dean's touch. "Why would I do that when you're so willing to take the brunt of it?"

"How thoughtful," Dean teases, taking another hit. This time when their mouths meet, it's because of Dean.

Sam's tongue darts out, flicking against Dean's lips. "Is this a part of my lesson, too?" he asks when he pulls away.

"Absolutely."

"Interesting lesson." Sam's so fucking hard he's aching for it. If he were sober, this might be the part where he'd be horrified with himself for throwing himself at Dean so blatantly, for assuming and not asking permission. But he’s _not _sober. Or horrified. All he can do is breathe in what Dean's giving him and stay in his space. All he can feel is _happy _and _content_. Sam shivers and eyes the weed in Dean's hand. "I think it's starting to work."

"Yeah? How are you feeling?"

Sam shrugs. "My head feels weird. Can't really concentrate on much right now."

Dean chuckles, giving Sam a push. "You're always weird."

"Wow, fuck you," Sam says, sticking out his tongue. "I'd rather be weird than a big jerk. You... Jerk."

"I'm not a jerk! Look how nice I'm being!"

"What's nice? Pushing me? Yeah, that's _real_ nice, Dean," Sam teases, gently kicking Dean with his foot.

"Hey now!" Dean scrambles behind Sam, the telltale sign he’s contemplating putting Sam in a headlock.

"Don't you dare!" Sam squeals, rolling away from Dean. "Fuck off!"

Dean chases after him and Sam shudders when Dean grabs his hips, cock throbbing in his jeans. "If you don't knock it off, I'll be forced to beat your ass!"

"I'd like to see you try," Dean shoots back. They're both on their sides and Dean's _definitely _the big spoon right now.

"I could get out of this if I really wanted to," Sam insists, then pushes his ass flush against Dean's crotch. Just to freak him out. Obviously. "I'll do more than try. I'll win!"

Dean only moans brokenly in reply, grip tightening on Sam's hips.

"Oh, fuck." Sam hadn't expected Dean to be hard, too. He doesn't know what to do with that. Okay, so partly a lie. He has ideas but they aren't necessarily smart ones.

Dean rolls his hips and now Sam's moaning too.

"Dean." Sam grinds his ass against Dean's clothed dick. "You fucking... need a spanking."

"Yeah?" Dean growls against Sam's ear. "And who's gonna give it to me, hmm?"

Sam tries to say _he_ would spank Dean. But he finds himself incapable of doing so. Not with Dean growling. It's turning his brain to mush. Okay, so the weed and alcohol turned him into a moron long before this moment, but the growling _really_ isn't helping.

"I don't know."

“I think_ you_ need a spanking." Dean’s hand goes to the front of Sam's jeans and he begins unbuttoning his pants.

“You're kidding," Sam says and starts to squirm. He still isn't _really _trying to get away, though. "Why? What'd I do?"

“You're being a brat,” Dean hisses and yanks Sam's pants down, landing a firm smack to Sam’s ass.

Sam yelps. "Isn't that my job?"

“Hell no.” Dean sits up then and drags Sam onto his lap, immediately going to town on Sam’s cheeks. Showing no mercy.

“Ow!" Despite Sam's complaining, his cock jerks and he lifts up to meet Dean's hand before rutting his cock against his brother, searching for friction. "Oh my God, Dean. Keep going. Fuck."

"You really like that, huh?" Dean asks, hitting Sam’s flaming ass again.

Sam nods, letting out an overwhelmed sob. He reaches behind himself to pull his asscheeks apart. "Can you hit my hole, too?"

“Jesus...Yeah, I can do that, Sammy." Dean clears his throat and his fingers smack Sam’s hole. "Fuck. You gonna come?"

In response, Sam does just that, making a mess all over his brother as he wails his name. "Dean, Dean, Dean!"

“Jesus fuck, Sammy,” Dean breathes, his fingers sliding over Sam's sensitive skin.

Oh, _God. _

Sam’s fucking mortified. Ready to hide in a hole for the rest of forever. Coming so fast... he hates it, now that it’s over. He keeps his eyes down and worries his lip. "Now's your chance to laugh at me."

“Laugh at you?" Dean asks, rolling his hips, cock pressing against Sam firmly. "I'm so hard I can't fucking think straight."

“I can't think straight either," Sam gasps, fucking _wrecked_. "You're so big."

“You mean my cock?”

Sam lets out a wounded noise and nods vehemently. "_Yes_. Are... are you gonna come, too?"

"God, I like your noises, Sammy.” Dean’s hand caresses Sam’s spine then travels down to his crack, touching Sam's hole. "I wanna put my cock in here.”

“Looking to pop all my cherries at once, I see." Sam pulls his ass cheeks apart again, giving Dean easier access to his virgin hole. "Will your dick even fit in here?"

“Shit! You’re not still…” Dean’s voice drifts off, pressing harder until just his fingertip breaches Sam. “Are you?”

“_Fuck._" Sam’s hole flutters on Dean’s fingertip and Sam swallows thickly. He'd be lying if he said he isn't scared. "Yeah. I am. And I... I really don't think you'll fit."

“You sayin’ you don't want me to try?" Dean asks, voice rough from obvious arousal.

"You can try. Just... I hope it works." Sam trembles with fear and want.

"Don't worry, I'll take care of you." Dean pats Sam's ass. "Get up for me. I gotta get some lube out of my bag."

Sam’s soft cock twitches in interest. "Okay," he breathes, rolling off of his brother.

Dean stumbles to his feet and roots through his bag for lube. When he finds it, he throws it on the bed. After a few heartbeats, Dean fiddles with the amulet before gently pulling it off and placing it on the worn-out motel table. The shirt comes off next, and Dean's not nearly as careful with it. He tosses it and doesn't even look to see where it lands. "You gonna get naked for me?" he finally asks.

Sam points to his mostly naked lower half. "What, that's not good enough? My most important hole is right here."

Dean laughs outright. "I wanna _see_ you. Come on, Sammy. Be nice to me.”

"If that's really what you want." Sam worries his lip, regarding Dean a moment before following suit, tugging his shirt off too.

“Yeah, look at you. So fucking pretty,” Dean says as he undoes his pants.

Sam makes an awkward noise as he resists the urge to cover his naked body. "Hurry up," he demands, ignoring Dean's compliment.

Dean rolls his eyes and plops back onto the bed. "Come on. Lay across here again,” he says, patting his lap.

Sam licks his lips and does what he’s told, humming happily when his bare skin touches Dean's. "Maybe the alcohol and drugs will make it all hurt less.”

Dean slicks up his fingers and rubs lube against Sam's hole. "You feel good, yeah?”

"Yes."

"Good. We can finish the joint if you want once you're sitting on my cock," Dean says and starts pressing his finger in.

Sam can't speak, can't reply. His first instinct is to try and get away from the finger sinking into him. It's fucking _weird_. Asses aren't made for this, he's sure of that now.

And yet... He isn't trying to escape. So. It clearly isn't awful.

Dean rubs the small of Sam's back as he starts to pump his finger in and out gently. After a few thrusts, he crooks his finger into what Sam can only guess is his goddamn prostate.

Sam keens, pushing into Dean's finger. Okay, maybe _that's _why anal sex is a thing. Jesus Christ.

"Have you done this before?" Sam asks, trying not to sound accusatory and jealous.

"A few times."

Sam almost growls but then Dean's touching him _there_ again. His mostly soft cock starts to react and stiffen. "Lucky them."

"You sound jealous." Dean presses a second finger against Sam's hole.

Sam lets out an unsure noise when he feels finger number two. "And _you_ sound amused by that possibility."

"It's pretty hot." Dean starts pressing the second finger in. "You're gonna have four of these in you before you can take me. I need you to tell me if it's too much."

Sam whimpers, clutching the bed beneath him. "What will happen if it's too much?"

"Then we take a break. Or I’ll suck your cock instead.”

"I already came once. You haven't," Sam points out breathily. "So shouldn't I suck _yours_ if it came to that?"

Dean moans softly. "You'd do that for me?" he asks as his fingers scissor Sam gently.

"Dean. You've got your fingers in my ass. I think this is a few steps above cocksucking," Sam sassily replies. "Of course I would, what the hell. Quit being dumb."

"Have you done it before?"

"No. I told you, I'm a virgin," Sam says with difficulty, his face flaming.

"Oh, God. It would be so sloppy and hot."

Sam bites back a whine, rolling his hips. "You sound really fucking turned on, Dean."

And God help him, Sam likes it. A lot.

"I am." Dean breathes, scratching his fingernails across Sam's ass. "_You_ turn me on."

Sam lifts into Dean's attention as his cock gets even harder. "_Fuck_. You turn me on, too. I can barely take it."

"Think you're ready for another finger?"

"We can try."

Dean removes his fingers and adds more lube then presses two back in. He fucks Sam like that a little before pressing the tip of a third finger in.

"Oh, fuck," Sam says in a strangled tone. A tremor goes through Sam's entire body and there’s an urge to crawl away. It was just so _much_. "Fucking hell."

Dean pulls the third finger back out, stroking his hand up and down Sam's back. "Breathe, baby."

Sam lifts his aching ass up. "Don't stop," he pants. "Want it."

Dean scissors his two fingers anyway, stretching him more and pressing against Sam's prostate before working in a third finger.

This time, Sam’s into it. _Very _into it.

"Oh my god." Sam rolls his hips, trying to get Dean's fingers deeper inside. "Tell me... tell me about the people you've fucked with your thick fuckin' dick," he says even though he isn't sure he actually wants to know.

"I fucked this guy on the football team once. Can't remember his name... Left his hole gaping."

"How... how did you leave it gaping?" Sam asks, scared and hopelessly turned on.

"Your muscles here," Dean says, using his fourth finger to touch Sam's rim. "Are meant to be closed. Obviously they can be worked open. Sometimes when you put something thick enough inside for long enough…” Dean’s voice trails off, which is fine by Sam. He gets the picture.

"Are you gonna leave me gaping, Dean?"

"I don't know."

"I hope you do," Sam rasps, shivering and leaking at the thought.

"Yeah? You wanna feel me tomorrow when you sit down?"

"I bet you'd like that."

"Yeah. Seein' you walk with a little limp. Knowing that I put it there."

Sam wails, fucking himself on Dean's fingers. Well. He tries to. It’s a bit difficult to do considering he’s laying across Dean's lap. "Pervert. You're like... a dirty old man somehow even though you're only in your early twenties."

Dean barks a laugh. "Nah, I just _really_ like the idea of popping your cherry.”

Sam can relate. He likes the idea a bit too much himself.

"Are you gonna fuck me or what?"

"Think you can take another finger for me?"

"Why can't you just fuck me? I don't care how much it hurts!"

"Well, I care," Dean replies firmly. "No way am I hurting you. So be patient." He gives Sam's ass a firm smack.

"Spankings aren't really a deterrent, Dean. Not sure why you did that."

Dean laughs. He pulls out his fingers and adds more lube before he starts to push four in slowly. "I did it _because _you like it."

Sam sobs at the fullness and rubs his face on the bed. "You're so mean."

"Quit being a little bitch."

"See, I think you're just trying to drive me crazy and make me beg," Sam declares, pouting again.

"You're almost ready,” Dean promises.

"Hurry."

Dean, unfortunately, does _not_ hurry. Sam's having a hard go of it keeping track of time but he knows this much. At Sam's demand, Dean's pace has slowed down even more; it’s fucking glacial.

"Dean, if you don't fuck me now, I'll tie you down and take care of it myself," Sam warns, looking up at him again.

“No, you won’t.” Dean tugs his fingers free and spanks him again. "Get on your back. I wanna see your face."

"No. I wanna do it while straddling you. Preferably with both of us sitting up. I wanna be able to look into your eyes when you fuck me. I wanna be able to kiss you as much as I want. Missionary is boring."

"How would _you _know, virgin?"

"_Dean_ -"

"All right, all right. Don't get your panties in a knot. Get up and we can try."

Sam kisses and nuzzles Dean's cock before doing as Dean asked, feeling devious.

"You sure you’re a virgin?" Dean asks and sits at the head of the bed.

"So, first you make fun of me for being a virgin and now… what? You think I'm a slut? Which is it?" He crawls over to Dean, bending down to sloppily mouth at his cock.

Dean's head falls back and his fingers slide into Sam's messy hair. _"Fuck_, Sammy."

Sam smiles against Dean's cock and gently tongues the tip of it. "I need to worship this sometime."

"You can worship it by sitting on it,” Dean growls as he tugs Sam's hair.

Sam gasps at the hair pull and sits up, shivery with desire as he stares at Dean directly in the eyes. "Say it again. Say what you want."

Dean leans in and kisses Sam hard. "I want you to ride my dick until you come on it."

"What if I can't? I already came. I want _you_ to come."

"Oh, I will. " Dean runs his hands up Sam's thighs and squeezes his hips.

"You're so fucking bossy," Sam pants, rubbing his ass against Dean's dick. "Even when you aren't saying anything."

Dean moans softly. "You like it.”

"You said we could finish the joint when I'm on your dick. Did you mean it?" Sam asks, nudging Dean's temple with his nose.

“Yeah, of course." Dean cups Sam's ass cheeks and spreads them apart. "Come on. My dick is aching for you."

Sam gives into his brother, sinking down on Dean's dick until just the head breaches him, letting out a soft cry.

“Fuck, you're tight.”

Sam yelps, his sore hole clenching on Dean's cock. He tries to sink further down onto it, but his ass isn't having it just yet. "Or maybe you've just got a monster dick, ever think of that? Fuck, are we sure it's gonna fit?”

“It’ll fit,” Dean gasps, stroking Sam’s hips and belly. "Just take your time. Relax.”

"How do you know it'll fit, though?" Sam worries his lip through his teeth and tries to relax. He wiggles on Dean's dick and sinks down another inch. He still has a long way to go but progress is progress.

"I've seen guys take _two _dicks once, Sammy, I _know_ you can take one."

Sam wiggles some more and finally slides the rest of the way down. "Your dick is fucking ridiculous," he breathes against Dean's mouth. "No one should have a dick this big. Fuck."

“How does it feel?"

Sam shivers. "It's intense. Why are you touching my stomach?"

“I wanted to see if I could feel my cock in you." He presses harder. "And it'll feel good for you too.”

Sam swallows thickly. "So? Do you feel it?"

"Yeah,” Dean rasps. He grasped one of Sam's hands and presses it up against his belly so he can feel for himself.

"Holy shit," Sam groans, rolling his hips. "Does this happen to everyone? Or is it ‘cause of how fucking huge you are?"

Dean nuzzles into Sam's neck and nips at the skin there. "No... Not everyone. But your belly is so flat and you're just so... Nnngh." He gives Sam's neck a real bite.

Sam keens, pushing into the contact greedily. "I'm just so what?"

"You've gotten so big. ‘Specially since that last growth spurt but you're still so sweet and supple and fuckable,” Dean says and rolls his hips up into Sam.

Sam lets out a needy noise, dragging his nails along Dean's arms and back. "I bet you say that to all the pretty girls."

“Yeah, but you’re my favorite.” Dean spanks Sam’s ass hard. “You gonna ride me, sweetheart?"

Sam trembles and shakes his head no. "You promised me the rest of the joint. I'd like to finish it before I go to town on your dick. Besides, it'll give me more time to get used to it."

Dean lets out a pathetic noise and presses his forehead against Sam's shoulder. His cock _throbs_ inside Sam. He reaches out to grab the joint, quickly re-lighting it. "You want it from the joint or from me?"

Sam teasingly rolls his hips, dirty and slow. "It's more fun taking it from you."

Dean lets out a wrecked sound and takes a deep hit from the joint. He holds it a moment before pulling Sam down from a dirty kiss and channeling the smoke into his mouth.

Sam continues his glacial pace, wanting to force more noises out of Dean. He coughs a bit at the slight burn from the smoke, then giggles. "You sound so fucking hot when you're desperate."

"I've been hard for a long time now Sammy and _you’ve_ come...I just need-" Dean huffs and thrusts up again. "I need you to _move_."

“But I _am_ moving."

Dean curls his hand tighter around Sam's waist. "So slow," he gasps and takes another hit of the joint. He thrusts up into Sam again as he breathes the drugs into Sam moments later.

"This is what you get for taking so long with my ass," Sam says sweetly, grinding on Dean.

“Are you sore?"

"I _was_ a virgin - so _yes_. I'm sore," Sam replies and giggles again. "S'what happens when you pop cherries, Dean."

"Yeah but you aren't aching. You didn't tear. I didn't _hurt_ you. _That’s_ why I took my time."

“Oh, I'm aching," Sam says, nipping Dean's bottom lip. "What point are you trying to make, hmm? That I should move faster for you?"

“No. You should be fucking thankful I took my time, you brat!"

“I'm thankful you're finally fucking me. I'm thankful I get to feel you."

They’re almost done with their weed. "Ready for another hit?"

"Yes," Sam says breathily. "Give it to me."

Dean reaches up, tangling his fingers into Sam's hair to pull him in for a kiss and gives him the smoke.

Sam kisses Dean back desperately, licking into Dean's mouth. At this point, he doesn’t even care about the weed. He just wants to melt into his brother.

When the blunt is done, Dean carefully sets it aside and puts his hands on Sam's hips. He thrusts up sharply then, groaning low, his head falling back a little in pleasure. Sam starts to bounce on Dean's cock in earnest. "I wanna roll you over and pound you.”

Sam whimpers, his traitorous dick leaking pre-come at the thought. "Do it."

Dean grips Sam's hips and rolls them. He presses Sam into the mattress for a kiss then slams back into him. Sam howls, wrapping his legs around Dean so he can hold on for dear life.

"You gonna come again for me, Sammy?”

Sam shivers, clenching Dean tighter. "I don't know yet."

Dean bites at Sam's ear lobe, tugging. "I'm getting closer,” he breathes hotly.

"Yes," Sam hisses, nails biting into Dean's skin. "I wanna feel it.”

Dean keeps his brutal pace, fucking deep and hard into his brother. It’s not long before he’s spilling into him.

"Thank you," Sam gasps, stroking his fingers through Dean's hair.

Dean kisses along Sam's jawline. "No, thank _you_."

Sam's dick is hard but he ignores it. "I would go shower but I don't trust myself not to fall and die right now. I might just lay here forever."

Dean sneakily starts stroking Sam's cock. "Maybe I can carry you to the shower after."

"Dean, you don't gotta do that," Sam gasps, wiggling at the sudden stimulation. "And I'm not a kid, I don't wanna be carried. I'll just shower later."

"What if I want to?" Dean asks. He presses his thumb along Sam's slit.

Sam whines and trembles. "What if you want to _what?" _

"Carry you to the bathroom," Dean replies and moves his hand to jack Sam again, cock still buried inside him.

"No," Sam tries to say firmly, but it’s kind of impossible with Dean _touching _him like this. "I already told you. I don't _want _to be carried. I'm not a _kid_. Deal with it."

"Okay." Dean rasps and leans down to bite one of Sam's nipples.

"Fuck," Sam yelps, squirming again. His hole clenches on Dean's softening cock _hard_.

Dean lets out a little gasp and finally pulls out of Sam, bending down and swallowing Sam down to the base of his cock.

Sam damn near _yells, _tears pricking at his eyes. "_Dean_," he says desperately, fisting his brother's hair. "Warn me next time, _fuck_."

Dean smiles up at Sam and slides through the come and lube, finding Sam’s prostate in no time.

That’s it. There’s no surviving after that. Sam sobs out his release, lifting his hips up and jams his cock further into Dean's mouth as Dean chokes on his come. Sam pants and lets out overwhelmed noises as he starts to come down, rubbing a hand over his face. "What the fuck, dude."

Dean pulls off with a gasp and wipes his mouth. "What?"

Sam growls and reaches out to pull Dean in for a messy kiss. "You're so stubborn. Said you didn't need to get me off. And you just kept going. You're so bad.”

“You're so fucking pretty when you come, Sam. I _had_ to see it again," Dean replies between kisses.

Sam sighs happily against Dean's mouth, saying nothing. He doesn’t need to.

* * *

The next morning, Sam wakes up and promptly wishes he hadn't. Dean's come is dried on his skin (which is _horrible_, Christ, he really should have showered before going to sleep) _and_ he has a headache.

"Fuck," Sam whines, mostly to himself. "I feel like roadkill."

"Sexy roadkill, though."

"Gross, Dean," Sam says, rubbing his forehead. "This is awful. I'm never drinking again," Sam complains, knowing full well it’s a lie. Drinking sucks. Being drunk doesn’t.

Dean chuckles and drags himself out of bed. Naked. He wobbles over to the bathroom and fills two glasses of water. He brings one to Sam and presses two Tylenol into his hand. "Drink the whole glass."

"Quit ordering me around," Sam grumbles but does what he’s told, not stopping until the glass is empty in hopes it would bring sweet relief. "Wow, I might throw up.”

“You're dehydrated," Dean announces and drinks down his own water.

“Gee, really?" Sam replies sassily. "Never could have guessed."

He notices Dean staring and it’s making his whole body come alive.

"Other than the migraine... How are you feeling?"

Sam's dick twitches and he wets his lips nervously. Thank fuck he has a blanket covering his lower half. "I'm fine. You?”

Dean gets on his own bed and pillows his head on his bicep, his eyes lingering on Sam’s... mouth? Fuck. "I'm good.”

"Good." Sam's breath hitches and he squirms under Dean's gaze. "I think I need a shower. Unless you wanna go first?"

"Go for it."

Sam rolls out of bed, trying to hide his hard cock and ignore his aching ass. The come stains on his body. "I'll make it quick."

Sam takes the fastest shower of his life, refusing to jerk off. He walks out of the bathroom mere minutes later. "Your turn."

When Dean’s showering and Sam’s dressed, the roar of the Impala's engine announces John's arrival home. He enters the motel room without knocking, nodding to Sam and walks over to the table, pausing only when he sees the partially consumed bottles of alcohol. He looks at Sam then, irritation evident on his face. “Damn waste of money... _you_ weren’t drinking, were you?"

Sam gives John a mean smile. "And what if I was? Apparently, it's a Winchester family trait. Might as well try it now. See why my daddy likes it so much."

“You put Dean up to this?”

Sam shrugs. No way is he gonna rat Dean out. "And if I did? You gonna hit me?"

"Watch that mouth of yours before it gets you into even more trouble.”

"Is that a threat?" Sam asks, sneering. He takes a few steps towards John - which is probably not the best idea (or even in the top five, really) that he's come up with in the past twenty-four hours. But, damn, this man can rile him up like no one else.

"Should it be?" John asks, not backing down as he stares at Sam.

Sam keeps moving in John's direction until he’s less than a foot away. "You don't scare me."

He knows it’s wrong. Down to his bones, Sam knows he will likely just provoke the old man - but he doesn't care. He's fucking tired. Tired of the fights. Tired of John's demands. Sam’s suffered enough - him _and _Dean.

"Then you're dumber than I thought. Going through this much booze and-" John sniffs the air. "Weed. What if something had happened when you were wasted?"

“Oh, something happened all right," Sam says and jabs John's chest with a finger. "But they were all good things. _Dean _was with me."

John catches Sam's wrist and twists it. Not enough to break it, but certainly enough to get Sam’s pulse rabbiting in his throat. Sam hisses but doesn’t try to extricate himself from John’s hold. "Did you bring a couple of girls back here? Mess around when you _should_ have been training and keeping your wits about you? Stinks like sex in here.”

"The most disturbing part about this is that you assume it was girls."

"I don't care _who_ it was, Sam. The point is that you pissed away all that money on booze and drugs. You boys let your guard down. That’s unacceptable,” John says, disgust in his tone as he aggressively releases Sam’s wrist.

“I don't regret it. And I'd do it again. Last night was one of the best nights of my life and I won't let you ruin it for me."

"It was?"

Sam’s eyes widen and he squeaks, turning to look at his brother, at _Dean_. He’s in the doorway with a towel around his hips. "Yeah. Dad was worried about what _could _have happened, but I really don't give a shit."

"That's your fucking problem, Sam. You don't give a shit. You _never_ do,” John growls.

"Dad-"

"Don't want to hear it, Dean,” John says, not taking his eyes off Sam.

"You're right. I _don't. _I just want to be _normal_. And _happy! _There is _nothing _wrong with that. Or at least there wouldn't be if I was in a stable household," Sam snaps back. "All I wanted was to live somewhere long enough to make real friends. All I wanted was a place to call home. Not a fucking motel room or a place to squat for a few weeks before moving on to the next hunt. A _real _home. And you couldn't even give me that - give _us _that! Fuck you.”

"You _know _why we move around, Sam.”

"Yeah? Well, I didn't _ask _for this! I wasn't given a _choice," _Sam says, fucking _enraged _now. He pushes on John's chest. "Mom is _dead. _No amount of hunting will bring her back. And revenge, if that’s what you’re after, is pointless. Get it through your fucking head! I don't care about hunting, I don't want to, and now that I'm an adult - you can't _make _me!"

John raises a hand and, for a brief second, Sam thinks he’s going to get hit after all. But Dad picks up the bottle of tequila instead and hurls it at the nearest wall. "I did my best with you boys. I taught you how to survive, you ungrateful little shit. You just gonna leave? And do what?"

Sam flinches. Really, he has been preparing for this, but it still has his pulse picking up. And Dean’s silent, a living statue. Not stepping in. Yet more proof that Sam needs to get the hell out of here. Sleeping with Dean hasn’t changed anything about this toxic environment, it’s no magic cure-all. Dean’s still going to make nice with John, something that doesn’t sit right with Sam. Even though he 100% understands why Dean does it, why he tries to mediate and keep the peace, it hurts. A lot.

"Like I'm telling you shit," Sam spits out, all venom. He gestures at the booze. "Have fun with the rest of the alcohol. I won't be drinking it."

"Both of you, calm down -"

"Boys, I want you to clean up this mess. Dean, get some clothes on," John says, cutting Dean off. "And you're damn right you won't be drinking any more of it, Sam."

"Nah, I'm going out for a walk," Sam says acidly and begins walking towards the door. "Maybe I'll help later if I'm feeling generous. But since I'm an ungrateful little shit, I'm sure you already knew this would happen."

"You walk out that door and you can sleep out in the car tonight," John says, low and dangerous.

Sam doesn’t bother replying. He simply storms out of the room. He doesn’t have a destination in mind, he just has to get out of there.

Thankfully, he doesn’t have to go far before coming across a park. Sure, he’s too old for this shit and hanging around a park is lame and a little creepy, but he needs a pick-me-up, dammit. So, he gets on the nearest swing and lazily moves his legs back and forth, closing his eyes as he enjoys the movement. Letting daydreams of escape and freedom wash over him.

* * *

"Hey, Sammy."

"How'd you find me?" Sam asks, biting his lip as he glances over at Dean. Logically, he knows it wouldn't be too difficult. There were only so many directions that made sense on foot. But the question comes out anyway.

"I'm a hunter.”

"True." Sam smiles despite everything and Dean grins right back. "Dean, you should come with me.”

Dean's smile falls away. "I can't do that to Dad. Do _you _really gotta go?"

Sam shoots Dean an irritated look. "Why the hell did you get me drunk if you were just gonna pull this shit? I thought you accepted that this was what I had to do."

"Best night of your life, huh? But not enough to make you stay?" Dean asks, stretching out his legs.

"Dean, that's not fair."

"Sure it is."

"Cute. But you realize I could use that logic against you too, right?" Sam asks, rolling his eyes. Because if he doesn’t stay mad, he’s going to cry and be vulnerable. And that’s so much worse. "You're still gonna do whatever Dad wants despite what happened last night, not what you want. We could get a place together... but you won't break up with him. Instead, you'd rather stay in a toxic, abusive environment. Am I getting this right? Clearly, last night wasn't a big thing for you if you won't come with me. Do you see how shitty this line of thinking is now?"

Dean sighs heavily and gazes up at the sky. "I'm not smart like you, Sam. I don't have a future out there. The only thing I'm good at is hunting."

"That's such bullshit," Sam insists, unmoved by Dean's words. "Come with me or don't. But I'm not staying. I want to be happy. I want both of us to be happy - and that's goddamn impossible around Dad. Don't you see that? Open your eyes! Why does it fucking matter that we're all he's got? We didn't ask to be born! We don't owe him our entire lives just because we're blood. We don't owe anybody anything."

"Please, Sammy.”

"Please, Dean," Sam tosses back at him. "I get it if you don't want to be around me. I won't and can't force you to go. But the offer is on the table."

“Of course I care! I wanna be around you. Fuck... I. I fucking _love_ you, Sam. I just... I can't leave Dad. You know how he is. He'll spiral and-"

"And what? Die? Is that what you think will happen if we fuck off somewhere else to be happy?" Sam demands, his chest and throat tight. "Because maybe we would be better off. Especially if you love me."

"Sam, Dad's family. I can't just abandon him."

Sam gets off the swing and stretches his arms out wide as he stares his brother down."Yeah? Well, I need you too! Away from here. If you come with me, you're free! Go ahead and continue hunting if you want - just fucking come with me!"

Dean sniffles and swipes angrily at his eyes, refusing to look at Sam. "We should stay outta Dad's hair tonight. Shoot some pool and make back some cash."

Sam's shoulders slump. So that’s it then.

"Yeah, okay. Hey, Dean?"

"Yeah?" Dean meets his eyes, albeit hesitantly.

Sam wants to yell, cry, and fucking beg. But he can’t do any of those things. Dean’s staying. Sam’s failed. He glances at the protective charm hanging on Dean’s neck. Will Dean still wear the amulet when he's gone? Will he hide it, pretend it doesn't exist?

Sam's lower lip wobbles as he watches Dean, tears pricking his eyes as he swallows the desperation choking him like a stone. It settles inside him, making its home there. For now. "I love you, too."

**Author's Note:**

> Tori thought the title ‘Cherry’ would be hilarious due to the cherry popping that happens in the fic. Holly agreed. Upon further contemplation, maybe that was a bad choice due to how much the ending hurts. Oops. 
> 
> Friendly reminder that this fic is a collab! Comments and kudos give Tori and Holly life. Feel free to let us know if any tags are missing!


End file.
